A fluorescent probe for copper and hypochlorite based on rhodamine hydrazide framework

Jung Won Yoon, Min Jung Chang, Seungwoo Hong, Min Hee Lee

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

A rhodamine derivative (1) was synthesized as a fluorescence turn-on probe for copper (Cu2+) and hypochlorite (ClO). The probe gave a fluorescence turn-on change at 587 nm with a color change from colorless to pink in the presence of Cu2+ or ClO ions in aqueous solution. It was found that the Cu2+ ion bound to 1 in a 1:1 stoichiometry and induced a spirolactam ring opening of the rhodamine moiety leading to a fluorescence turn-on, confirmed by Job's plot, ESI-Mass, and 1H NMR analyses. In the presence of ClO ion, probe 1 underwent a hypochlorite-mediated oxidation and hydrolysis to produce a ring-opened rhodamine B with a fluorescence enhancement. However, these changes were not monitored in case of other metal ions, anions, and reactive redox species. In addition, probe 1 can readily react with the ClO to provide a distinct fluorescence enhancement along with a pink color even in the presence of various competitive species.

Original languageEnglish
Pages (from-to)3887-3893
Number of pages7
JournalTetrahedron Letters
Volume58
Issue number40
DOIs
StatePublished - 2017

Bibliographical note

Funding Information:
This research was supported by the Korean National Research Foundation (NRF) ( 2015R1C1A2A01054496 , M.H.L).

Publisher Copyright:
© 2017 Elsevier Ltd

Keywords

  • Copper detection
  • Fluorescence turn-on
  • Hypochlorite detection
  • Rhodamine hydrazide

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